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(2004)Directed by John Hamburg90 min · PG-13Comedy, Romance

“For the most cautious man on Earth, life is about to get interesting.”

Reuben Feffer (Ben Stiller) has spent his whole life playing it safe, and his job is judging how much risk other people can take on. Then he runs into his old classmate Polly Prince (Jennifer Aniston), who lives for the moment and does whatever the moment says. John Hamburg sets the two against each other, and Reuben keeps trying to loosen up, even as his ex-wife Lisa (Debra Messing) returns wanting him back.